Tag: M.W=100-200

Electric Literature of 69395-13-7,Some common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, molecular formula is C9H9NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

PREPARATION 13 Preparation of 4-carbamoylphenethyl bromide and 4-cyanophenethyl bromide STR36 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give 4-carbamoylphenethyl bromide as a colourless solid, yield 0.47 g, m.p. 152-153.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Hydroxyethyl)benzonitrile, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5340831; (1994); A;,
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Synthetic Route of 39581-21-0, The chemical industry reduces the impact on the environment during synthesis 39581-21-0, name is N-Butyl-2-cyano-acetamide, I believe this compound will play a more active role in future production and life.

Example 11. Synthesis of 1,5-dibutyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (AA11) [Show Image] Under the nitrogen gas atomosphere, a mixture of 28% sodium methoxide methanol solution (39 mL, 202 mmol) and ether (260 mL) was cooled to 3C in an ice bath, and the mixture of 2-heptanone (22.84 g, 200 mmol) and ethyl formate (16.15 g, 218 mmol) was dropped in about 20 minutes. After that, being stirred at the same temperature for 30 minutes, then the mixture was returned to be at room temperature and was further stirred for 20 hours afterwards. The precipitated product was removed by filtration and washed enough with ether (about 620 g). The mother liquor and the washing layer were combined and concentrated to give a crude product of 29.34 g. This crude product was repeatedly washed with hexane and ether, and powdered yellow ocher sodium salt of 3-[1-hydroxymethylidyne]-heptan-2-one (11.33 g, 34.5%) was obtained. This salt (2.13 g, 13 mmol) was suspended in DMF (10 mL), and n-butylcyanoacetamide (1.40 g, 10mmol), acetic acid (0.75 mL, 13.1 mmol), piperidine (0.20 mL, 2.02 mmol) were added in order at room temperature, and the mixture was refluxed at 135C for 7 hours. After that, the reaction mixture was let alone at room temperature for 13 hours and then poured into ice water, and the obtained mixture was extracted with ethyl acetate two times. The organic layer was washed with diluted hydrochloric acid one time and with water two times, and then died with anhydrous magnesium sulfare. The solvent was removed by distillation under reduced pressure, and a red oily crude product of 2.03 g was obtained. This crude product was refined by the silica gel chromatography, and the desired 1, 5-dibutyl-6-methyl-2-oxo-1, 2-dihydropyridine-3-carbonitrile (AA11, 420 mg, 17.3%) and 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile (230 mg, 9.4%) were obtained. AA11 NMR:(CDC13) 0.95 (t, 3H, J=6.9, 0.98 (t, 3H, J=6.9), 1:5-1.7 (m, 8H), 2.42 (s, 3H), ca 2.4 (m, 2H), 4.08 (2H, m), 7.57 (1H, s)) 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile NMR: (CDCl3) 0.94 (t, 3H, J=6.8), 0.98 (t, 3H, J=7.2), 1.3-1.7 (m, 10H), 2.66 (m, 2H), 4.04 (m, 2H), 6.11 (ABd, 1H, J=7.5), 7.67 (ABd, 1H, J=7.5)) was obtained.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Butyl-2-cyano-acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIONOGI & CO., LTD.; EP1806342; (2007); A1;,
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Electric Literature of 6136-93-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6136-93-2, name is 2,2-Diethoxyacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) To a solution of sodium methoxide (3.54 ml of a 25% wt. solution in methanol, 15.5 mmol) in methanol (80 ml) was added diethoxyacetonitrile (215 ml, 155 mmol) and the reaction mixture stirred for 4 hours at room temperature. Solid carbon dioxide was added and most of the methanol was removed in vacuo. Diethyl ether (30 ml) was added and the sodium carbonate removed by filtration. The residue was concentrated to afford methyl diethoxyacetimidate as a colourless oil (22 g, 92% yield) which was used with no further purification. MS (+ve ESI): 162 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,2-Diethoxyacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US7235559; (2007); B1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4640-66-8, name is 4-Chlorophenacylcyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H6ClNO

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1885-38-7, name is (E)-Cinnamonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (E)-Cinnamonitrile

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1885-38-7.

Reference:
Article; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
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Application of 69395-13-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 69395-13-7 name is 4-(2-Hydroxyethyl)benzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-(2-hydroxyethyl)benzonitrile (10.0 g, 67.94 mmol) in CH2Cl2 (175 mL) at 0 C. was added Et3N (11.36 mL, 8.25 mmol) and MsCl (6.31 mL, 81.53 mmol). After stirring at 0 C. for 3.5 hours, the reaction was poured into water (100 ml) and separated. Organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Crude residue was dissolved in DMF (100 mL) and NaN3 (9.15g, 140.72 mmol) and water (5 mL) were added. The resulting solution was heated to 125 C. After overnight stirring at 125 C., the crude reaction mixture was cooled, diluted with EtOAc (200 mL) and poured into water (150 mL). Organic layer was washed with water (5×150 mL), dried over sodium sulfate, filtered, and concentrated to give 4-(2-azidoethyl)benzonitrile which was used without purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Hydroxyethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Su, Dai-Shi; Bock, Mark G.; US2005/20591; (2005); A1;,
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These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 5-Amino-2-fluorobenzonitrile

carboxylate as an off-white powder (382 mg). Methyl 3-chloro-1-methyl-4-[[1- (trifluoromethyl)cyclobutyl] sulfamoyl]pyrrole-2-carboxylate (150 mg, 0.4 mmol) and 5-amino- 2-fluorobenzonitrile (0.52 mmol) were dissolved in dry THF and cooled to 0C. Lithiumbis(trimethylsilyl)amide (1.24 mL, 1 M in THF, 1.24 mmol) was added dropwise and the reaction mixture was allowed to reach room temperature. After 1 hour lithium bis(trimethylsilyl)amide (0.5 mL, 1 M in THF, 0.5 mmol) was added and the reaction mixture was stirred for another hour. The volatiles were removed under reduced pressure and the residue was purified on silica gel using a heptane to EtOAc gradient. The collected fractions were evaporated todryness and the residue was crystallized from a heptane/EtOAc mixture yielding compound 221(91 mg) as off-white powder. Method D: Rt: 1.95mm mlz: 477.1 (M-H) Exact mass: 478.0. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.75 – 1.88 (m, 2 H), 2.25 – 2.37 (m, 2 H), 2.41 – 2.48 (m, 2H), 3.79 (s, 3 H), 7.56 (t, J=9.1 Hz, 1 H), 7.68 (s, 1 H), 7.99 (ddd, J=9.2, 4.8, 2.6 Hz, 1 H), 8.20(dd, J=5.7, 2.6 Hz, 1 H), 8.61 (s, 1 H), 10.67 (s, 1 H).

The synthetic route of 5-Amino-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6FN

To a heterogenous solution of 3-fluoro-4-methyl-benzonitrile (5 g, 37.0 mmol) in ethanol (125 mL) at 25C was added hydroxylamine hydrochloride (5.14 g, 74 mmol) and triethylamine (10.3 mL, 74 mmol). The reaction mixture was heated at 80C for 1 hour. After cooling to room temperature volatiles were removed under reduced pressure thus affording a white gum that was used in the next step without any purification. LC/MS (Method A) retention time = 0.25 minutes, 169.3 (M+H). (0416) NMR (400 MHz, DMSO-de) delta ppm: 7.44 (t, 2H), 7.32 (d, 1 H), 5.85 (brs, 2H), 4.50 (brs, 1 H) 2.24 (s, 3H). (0417) 9F NMR (400 MHz, DMSO-de) delta ppm: -1 14.46 (s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 170572-49-3.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (111 pag.)WO2018/219773; (2018); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 39581-21-0 as follows. Recommanded Product: N-Butyl-2-cyano-acetamide

General procedure: A mixture ofan aromatic aldehyde 1a-1f (1 mmol) with N-butyl-2-cyanoacetamide 2 (1 mmol) in ethanol (5 mL) wasrefluxed for 2 h, after which phthalhydrazide 3(1 mmol) was added to the mixture and refluxingcontinued for 3 h more. Upon completion of theprocess, according to TLC, the mixture was cooled toroom temperature and the precipitate was filtered off.The crude product was crystallized from ethanol togive the respective compound 4a-4f.

According to the analysis of related databases, 39581-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elmi-Mehr; Davoodnia; Pordel; Russian Journal of General Chemistry; vol. 88; 12; (2018); p. 2595 – 2600;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 628-20-6, name is 4-Chlorobutyronitrile, A new synthetic method of this compound is introduced below., COA of Formula: C4H6ClN

A solution of 2- (1-methyl-1H-pyrazol-4-yl) -7- (piperidin-4-yl) -5 – ((2- (trimethylsilyl) ethoxy) -5H-pyrrolo [2,3-b] pyrazine (130 mg, 0.31 mmol)Of acetonitrile (8 mL)Potassium carbonate (110 mg, 0.79 mmol) was added sequentially to the solution,Potassium iodide (10 mg, 0.06 mmol) and4-chlorobutyronitrile (0.05 mL, 0.5 mmol)The reaction was heated at 50 C for 24 hours,Diluted with water (20 mL), extracted with dichloromethane (20 mL x 3), dried over anhydrous sodium sulfate and concentrated column chromatography (dichloromethane / methanol (v / v) = 8/1)120 mg of a yellow oil was obtained in a yield of 79.40%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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